Sulfuric Acid → HCID 69507129, compound

Participants

Reaction Steps

To a stirring solution of N-[2-(2,2-dimethoxy-ethylamino)-ethyl]-2-hydroxy benzamide (300 mg, 1.11 mmol) in CHCl3 (100 mL) was added conc H2SO4 (2 mL). The reaction was refluxed overnight, then cooled to room temperature then poured into a mixture of ice-saturated NaHCO3 solution. The mixture was extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine, dried on MgSO4, and conc in vacuo to yield a yellowish oil. The oil was then purified by chiral HPLC using an OD column with 10% iPrOH in heptane to yield 50 mg of the R enantiomer as white solid, MS (ESI) 205 (M+H), and 56 mg of the S enantiomer as white solid, MS (ESI) 205 (M+H).

Provenance & Evidence